GB2346144A - Hemoglobin with chemically introduced disulfide cross-links and preparation thereof - Google Patents

Hemoglobin with chemically introduced disulfide cross-links and preparation thereof

Info

Publication number
GB2346144A
GB2346144A GB0010464A GB0010464A GB2346144A GB 2346144 A GB2346144 A GB 2346144A GB 0010464 A GB0010464 A GB 0010464A GB 0010464 A GB0010464 A GB 0010464A GB 2346144 A GB2346144 A GB 2346144A
Authority
GB
United Kingdom
Prior art keywords
hemoglobin
cross
linked
cysteinyl
bis
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
GB0010464A
Other versions
GB0010464D0 (en
Inventor
Xianfeng Li
Ronald H Kluger
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Innovations Foundation of University of Toronto
University of Toronto
Original Assignee
Innovations Foundation of University of Toronto
University of Toronto
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Innovations Foundation of University of Toronto, University of Toronto filed Critical Innovations Foundation of University of Toronto
Publication of GB0010464D0 publication Critical patent/GB0010464D0/en
Publication of GB2346144A publication Critical patent/GB2346144A/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/095—Compounds containing the structure P(=O)-O-acyl, P(=O)-O-heteroatom, P(=O)-O-CN
    • C07F9/096—Compounds containing the structure P(=O)-O-C(=X)- (X = O, S, Se)
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
    • C07C323/59—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton with acylated amino groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/795—Porphyrin- or corrin-ring-containing peptides
    • C07K14/805—Haemoglobins; Myoglobins
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Molecular Biology (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Peptides Or Proteins (AREA)

Abstract

Hemoglobin cross-linked with disulfide linkages at sites external to the native globin chains is prepared by reacting hemoglobin with site-directed reagents exemplified by N,N'-bis Cbz-cysteinyl bis (methyl phosphate). Reaction with deoxy hemoglobin produces two main products: cross-linked hemoglobin as the bis cysteinyl amide of the e -amino group of the side chain of Lys-82 of the two b subunits, and modified but non-cross-linked hemoglobin that has each of the same amino groups modified as the cysteinyl amide. Disulfide cross-linked hemoglobin has a variety of uses. The disulfide bonds can be cleaved with reducing agents to give terminal sulfhydryl groups, useful in chemical bonding to sulfhydryl group-containing biochemically active compounds to form conjugates thereof for drug delivery. Hemoglobin cross-linked through disulfide bonds can be formed from the sulfhydryl group terminated reduction products, for use as a hemoglobin-based oxygen carrier.
GB0010464A 1997-11-03 1998-11-03 Hemoglobin with chemically introduced disulfide cross-links and preparation thereof Withdrawn GB2346144A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US6412297P 1997-11-03 1997-11-03
PCT/CA1998/001020 WO1999023065A1 (en) 1997-11-03 1998-11-03 Hemoglobin with chemically introduced disulfide cross-links and preparation thereof

Publications (2)

Publication Number Publication Date
GB0010464D0 GB0010464D0 (en) 2000-06-14
GB2346144A true GB2346144A (en) 2000-08-02

Family

ID=22053712

Family Applications (1)

Application Number Title Priority Date Filing Date
GB0010464A Withdrawn GB2346144A (en) 1997-11-03 1998-11-03 Hemoglobin with chemically introduced disulfide cross-links and preparation thereof

Country Status (4)

Country Link
AU (1) AU1015699A (en)
CA (1) CA2308277A1 (en)
GB (1) GB2346144A (en)
WO (1) WO1999023065A1 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0125793D0 (en) * 2001-10-26 2001-12-19 Panzeri Ezio Method
US7235639B2 (en) 2003-04-23 2007-06-26 Ezio Panzeri Hemoglobin conjugates
KR20240015482A (en) * 2022-07-27 2024-02-05 삼성에스디아이 주식회사 Positive electrode, and rechargeable lithium battery including the same

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5399671A (en) * 1992-11-18 1995-03-21 Kluger; Ronald Specifically crosslinked hemoglobin with free functionality

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5399671A (en) * 1992-11-18 1995-03-21 Kluger; Ronald Specifically crosslinked hemoglobin with free functionality

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Bioconjugate Chem., 1997, Vol. 8(6), pages 921-926 *

Also Published As

Publication number Publication date
WO1999023065A1 (en) 1999-05-14
AU1015699A (en) 1999-05-24
GB0010464D0 (en) 2000-06-14
CA2308277A1 (en) 1999-05-14

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Legal Events

Date Code Title Description
WAP Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1)